DIAZABOROLIDINES, A NEW CLASS OF ENANTIOSELECTIVE ORGANOBORON CATALYTIC AGENTS

被引:15
作者
FROELICH, O [1 ]
BONIN, M [1 ]
QUIRION, JC [1 ]
HUSSON, HP [1 ]
机构
[1] UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,CHIM THERAPEUT LAB,CNRS,URA 1310,F-75270 PARIS 06,FRANCE
关键词
ENANTIOSELECTIVE REDUCTION; DIAZABOROLIDINE; CHIRAL ALCOHOL; CATALYTIC REDUCTION; DIAMINE;
D O I
10.1016/S0957-4166(00)80097-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Diazaborolidines 6 and 9, derived from 2-aminomethyl-piperidine, have been prepared in an optically pure form from 2-cyano-6-phenyl oxazolopiperidine 3. The best results for the asymmetric reduction of acetophenone (yield>95%, 72% ee) have been obtained with BH3.Me2S in the presence of 9a as a chiral catalyst.
引用
收藏
页码:2335 / 2338
页数:4
相关论文
共 18 条
[1]  
Bonin M., 1991, ORG SYNTH, V70, P54
[2]   ORGANOBORANES .39. CONVENIENT PROCEDURES FOR THE PREPARATION OF METHYLBORONIC ACID AND TRIMETHYLBOROXIN [J].
BROWN, HC ;
COLE, TE .
ORGANOMETALLICS, 1985, 4 (05) :816-821
[3]   ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY A CHIRAL OXAZAPHOSPHOLIDINE BORANE COMPLEX [J].
BRUNEL, JM ;
PARDIGON, O ;
FAURE, B ;
BUONO, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :287-288
[4]   AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].
COREY, EJ ;
SHIBATA, S ;
BAKSHI, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863
[5]   A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION [J].
COREY, EJ ;
LINK, JO .
TETRAHEDRON LETTERS, 1989, 30 (46) :6275-6278
[6]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[7]   A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S ;
CHEN, CP ;
SINGH, VK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926
[8]  
FROELICH O, UNPUB
[9]   ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH CHIRAL ALKOXY-AMINE-BORANE COMPLEXES [J].
HIRAO, A ;
ITSUNO, S ;
NAKAHAMA, S ;
YAMAZAKI, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (07) :315-317
[10]   ASYMMETRIC REDUCTION OF ALIPHATIC-KETONES WITH THE REAGENT PREPARED FROM (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL AND BORANE [J].
ITSUNO, S ;
ITO, K ;
HIRAO, A ;
NAKAHAMA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :555-557